Myo-Inositol-l-phosphate

For all the substrates discussed so far the peptide catalysts employed had to differentiate between enantiomeric substrate molecules. Miller et al. subsequently screened peptide libraries for members able to selectively functionalize enantio-topic hydroxyl groups of meso inositols. In particular, they were able to convert myo-inositol 35 to either monophosphorylated D-myo-inositol-l-phosphate 37 or d-myo-inositol-3-phosphate ent-37 in high yield and excellent ee (98% Scheme 12.18) [38, 39], This remarkable result was achieved by use of either of the penta-... 

Loewus, M.W., 1977, Hydrogen isotope effects in the cyclization of D-glucose-6-phosphate by myo-inositol-l-phosphate synthase. J. Biol. Chem. 252 7221-7223. 

Majumder, A.L., Johnson, M.D., and Henry, S.A., 1997, lL-myo-inositol-l-phosphate synthase. Biochim. Biophys. Acta 1348 245—256. 

Majee, M., Maitra, S., Dastidar, K.G., Pattnaik, S., Chatteijee, A., Hait, N.C., Das, K.P., and Majumder, A.L., 2004, A novel salt-tolerant L-myo-inositol-l-phosphate synthase from Porteresia coarctata (Roxb.) Tateoka, a halophytic wild rice Molecular cloning, bacterial overexpression, characterization, and functional introgression into tobacco-conferring salt tolerance phenotype. J. Biol. Chem. 279 28539-28552. 

Yoshida, K.T., Wada, T., Koyama, H., Mizobuchi-Fukuoka, R., andNaito, S., 1999, Temporal and spatial patterns of accumulation of the transcript of myo-inositol-l-phosphate synthase and phytin-containing particles during seed development in rice. Plant Physiol. 119 65-72. 

Byun, S.M., Jenness, R., Ridley, W.P., and Kirkwood, S., 1973, Stereospecificity of D-glucose-6-phosphate - 11-myo-inositol-l -phosphate cycloaldolase on hydrogen-atoms at C-6. Biochem. Biophys. Res. Commun. 54 961-967. 

Jin, X., Foley, K.M., and Geiger, J.H., 2004, The structure of the lL-myo-inositol-l-phosphate synthase-NAD-2-deoxy-D-glucitol 6-(E)-vinylhomophosphonate complex demands a revision of the enzyme mechanism. J. Biol. Chem. 279 13889-13895. 

Chemoenzymatic strategies were recently also applied for the preparative-scale synthesis of the very rare and expensive research biochemicals D-myo-inositol-l-phosphate, and D- and L-l,3,4,5-myo-inositol tetrakisphosphates [127,167]. The approach uses commercial lipase from Pseudomonas sp. for the regio- and enantioselective acetylation (in vinyl acetate) of 4,6-di-O-benzyl-myo-inositol to lD-l-acetoxy-4,6-di-0-benzyl-myo-inositol (intermediate for D-IP,). and lipase from Candida antarctica for the enantioseparation of racemic 2,6-dibenzyl-myo-inositol by enantioselective C5-acetylation (in the synthesis of D- and L-1,3,4,5-IP4) (Fig. 12). 

Twenty inositol phosphodiester derivatives 104 have been prepared by reaction of inositol 1,2-cyclic phosphates with the corresponding alcohol catalysed by phosphatidylinositol-specific phospholipase The heterocycle, quercetin, has been rendered more water soluble by conjugation through a 1-O-succinyl-myo-inositol-L-phosphate linkage. ... 

Sculimbrene BR, Miller SJ (2001) Discovery of a catalytic asymmetric phosphorylation through selection of a minimal kinase mimic a concise total synthesis of D-myo-inositol-l-phosphate. J Am Chem Soc 123 10125-10126... 

The preparation of D.L-myo-inositol-l-phosphate-4,5-pyrophosphate from myo-inositol 1-phosphate-4,5-bisphosphorothioate by treating the latter with NBS has appeared. ... 

Nicotinamide adenine dinucleotide (9) Purification of myo-inositol-l-phosphate synthase 87... 

A short synthesis of D-myo-inositol-l-phosphate from myo-inositol involving... 

The Miller group was the first to report catalytic asymmetric phosphorylation of alcohols, in 2001 [81]. They reported that D-myo-inositol-l-phosphate 82 could be prepared with high levels of enantiomeric purity by the ASD of 2,4,6-tribenzyl-myo-inositol (81) using diphenyl(chloro)phosphate and triethylamine in toluene at 0°C catalyzed by 2mol% of pentapeptide 79, which contains an N-terminal TT-methyl histidine residue as the nucleophile (Scheme 41.29). 

Eisenberg, Jr. F., and A.H. Bolden D-Myo-inositol-l-phosphate, an intermediate in the biosynthesis of inositol in the mammal. Biochem. Biophys. Research Commun. 21, 100 (1965). 

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